Seemingly lopsided trades where the "loser" ended up winning the deal

LeafsNation75

Registered User
Jan 15, 2010
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Exactly.

If you're going to factor the Leafs getting Matthews as part of the Kessel trade, then almost every big trade in NHL history needs to be reevaluated and recalculated. Picking through the consequences of a trade is usually difficult enough without the butterfly effect of future events.
The thing is when others always brought up the Kessel trade from Boston to Toronto it was mentioned how the Bruins won the Stanley Cup in 2011 as a major reason to say they won the trade. However when Leafs fans liked to point out them being able to finish last place overall in 2016, being able to draft Auston Matthews because of that and trading for Frederik Andersen with Pittsburgh's 1st round pick in 2016 due to them trading Kessel to the Penguins, we were told those things had nothing to do with trading him away.
 

PsYcNeT

The No-Fun Zone
Jan 24, 2007
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Nieuwendyk for Iginla & Millen is debatable because ultimately Nieuwy won a cup with Dallas in '99 (and was the MVP), but at the time the trade was a reaaaaaaaaaaaaaaaaaaaally lopsided in favor of Dallas.
 
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LeafsNation75

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Jan 15, 2010
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I think that, in the end, we kind of won the Phnaeuf trade
I guess you can say Toronto also won the Phaneuf trade when they sent him to Ottawa because they did not have to retain any of his contract and last season when Ottawa traded Phaneuf to Los Angeles, the Senators retained $1,750,000 of his contract.
 

Fig

Absolute Horse Shirt
Dec 15, 2014
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How was the Kipper for the 2nd deal with SJS viewed back in the day? This deal is often touted as a win/win now, but it's a little known fact that Sutter actually wanted Toskala over Kipper at first and only took Kipper when that deal was refused. Sutter settled and ended up getting the significantly better of the two goalies he was targeting.

Although much more minor, I think I'd say the Shinkaruk for Granlund deal was like this. Many Vancouver fans were livid at the time, but they still have the more useful player. We will have to see what happens with Rychel, but Shinkaruk was quite close to considering Europe this offseason. Though... we would have lost Granlund for nothing anyways if we tried to keep him, so is this sorta a win/win since we still have something on the farm?

Also Van/Calgary, the same could be said of the Baertschi/2nd trade. I feel like we are ahead on that one now with Andersson, but Barts for a 2nd hurt at the time, especially to a division rival.
 

NyQuil

Big F$&*in Q
Jan 5, 2005
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I guess you can say Toronto also won the Phaneuf trade when they sent him to Ottawa because they did not have to retain any of his contract and last season when Ottawa traded Phaneuf to Los Angeles, the Senators retained $1,750,000 of his contract.

We got a pretty deep playoff run out of it.

I’m not overly perturbed.

We also got rid of a bunch of spare parts.
 

Critical13

Fear is the mind-killer.
Feb 25, 2017
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Meh, that's like saying it was a good idea to trade for Matt Duchene because the chemistry of our team tanked and we ended up with really good lottery odds that allowed us to draft Rasmus Dahlin.

Only we didn't get Rasmus Dahlin, we didn't even get Svechnikov, because we weren't lucky like the Toronto Maple Leafs.

Toronto has made some smart moves but drafting generational players via the luck of the lottery isn't something I give them a lot of credit for.

You shouldn't, Matthews isn't a generational player.
 
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blankall

Registered User
Jul 4, 2007
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Schneider for Bo Horvat seemed like a NJ win at the draft a few yrs ago.

Schneider had a lackluster season, but killed it in the playoffs. Assuming he is injury free, he looks like he's set to rebound to being one of the best goalies in the league again.

Horvat had 44 points last season.

If Schneider plays anything like he did in the playoffs in the regular season, this trade is going to look horribly lopsided again.
 

socko

Registered User
Nov 26, 2013
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Agreed.

Phil was never a franchise player, he was miscast and it's hard to keep those guys around when you're trying to change the character of a team. They'll usually be associated with that previous era.

If you could look at my post history, I was always pretty favourable with respect to Kessel, even when he was with the Leafs.

I just felt that a finesse winger can't be the guy that leads the team to a Cup. I think Montreal figured that out too.

Ironically, he's the kind of guy that could have been brought in now (like Marleau) if he hadn't had that existing history with the team.
The Phil Kessel you see today is not the player Phil Kessel was in his prime. In Pittsburgh, he's basically a PP specialist. He's Dave Andreychuk. In Toronto, he terrorized opponents with his speed and shot. That appears to be mostly gone.
 

NyQuil

Big F$&*in Q
Jan 5, 2005
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Ottawa, ON
The Phil Kessel you see today is not the player Phil Kessel was in his prime. In Pittsburgh, he's basically a PP specialist. He's Dave Andreychuk. In Toronto, he terrorized opponents with his speed and shot. That appears to be mostly gone.

I was thinking more about the old Phil Kessel coming to the Leafs now instead of when he did.
 

King Mapes

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Feb 9, 2008
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I don't think a lot of people would say the Leafs "won the trade" the way it's described by the OP, however I would say they did a lot better when they traded Phil Kessel to Pittsburgh than they get credit for. Trading him made it easier for them to finish last place overall in 2016, getting the best draft lottery odds for Auston Matthews, getting Kaspari Kapanen who scored the tying goal on the night they cliched a playoff spot in 2017 and trading Pittsburgh's 2016 1st round pick for Frederik Andersen.
I know what you're trying to say but that's a clear win-win. Helped Pens win a cup and that kickstarted the Leafs turn around.
 

LeafsNation75

Registered User
Jan 15, 2010
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Toronto, Ontario
I know what you're trying to say but that's a clear win-win. Helped Pens win a cup and that kickstarted the Leafs turn around.
I agree. However I remember others trying to downplay and ignore the after effects on the Leafs side. Finishing last place overall and getting Auston Matthews as a result and trading Pittsburgh's 1st round pick for Frederik Andersen. From what I recall they said those things had nothing to do with the trade itself and the Leafs clearly lost it since Kessel was the best player involved and winning the Stanley Cup in 2016.
 

Nico Hischier

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Nov 22, 2017
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What about the conacher and Ben bishop trade between Tb and ott. At the time it looked like conacher was about to beast and Bishop was just some tall goalie
 

socko

Registered User
Nov 26, 2013
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Martinez, GA
The best example I have of this doesn't come from hockey. The Detroit Pistons traded Grant Hill for Ben Wallace because they didn't want to lose him for nothing. Grant Hill was a NBA superstar. Wallace was nothing.
 

Alwalys

Phu m.
May 19, 2010
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How was the Kipper for the 2nd deal with SJS viewed back in the day? This deal is often touted as a win/win now, but it's a little known fact that Sutter actually wanted Toskala over Kipper at first and only took Kipper when that deal was refused. Sutter settled and ended up getting the significantly better of the two goalies he was targeting.

it was viewed as not much of anything because to the sharks kipper and toskala were both backups to nabby and were not threatening for the starting job. vlasic made the team at 19 and has been a stud ever since so there wasn't much time period at which there would have been any regret.
 
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